The 15 Greatest Musical Guest Stars In ‘Simpsons’ History

From when it first aired in 1989, The Simpsons has hosted an absolutely dazzling array of musical guest stars: from classic artists being presented to a new generation of 90s kids, to contemporary “of-the-era” stars crossing over onto the world’s biggest animated show.

Here’s an attempt to wrap our head around this endless list of cameos, ranked merely by how funny and how memorable their appearances were on the show (not as musicians).

15: Red Hot Chili Peppers

In 1993’s “Krusty Gets Kanceled,” Springfield’s premiere clown loses his show, but Bart and Lisa rally Krusty’s gaggle of celebrity friends: Johnny Carson, Hugh Hefner, a fiercely eco-conscious Bette Midler, and Luke Perry for a star-studded comeback special.

Bart and Lisa also snag the Red Hot Chili Peppers by smuggling them out of a poorly-planned gig at Moe’s. Anthony Kiedis tells Moe, “you told our agent this place holds 30,000 people,” to which Moe answers, “It does. We had 30,000 here last night. Now play.”

The band performs “Give It Away” on the Krusty special, and when the network has a problem with their lyrics, they’re all too happy to take Krusty’s excellent suggestion:

The band shows up to Moe’s in their underwear for the afterparty, and Flea screams, “Hey Moe!,” which wasn’t really in the script, but rather, a snippet of Flea messing around in the voiceover booth that they ended up using.

14: Aerosmith

In the classic “Flaming Moe’s” episode, Aerosmith made a more conventional-than-usual guest appearance on The Simpsons, highlighted by an unmistakable, frantically-animated Steven Tyler:

When Moe’s bar explodes in popularity thanks to a drink Homer invents, the bar is soon packed with customers – including one actually named “Hugh Jass,” thwarting Bart’s crank-call attempt, and Moe lures Aerosmith into an impromptu performance with the promise of free pickled eggs.

The episode aired in 1991, and the band would go on to have their first-ever No.1 album, Get A Grip, two years later, confirming that the “Moe Bump” is real.

13: James Taylor

“Wow… former president James Taylor.”

That’s Homer’s reaction when NASA hires the folk icon to play for him and Buzz Aldrin during their ill-fated mission to send a common man to space. But while the ship is in danger, Aldrin tells Taylor, “this isn’t the best time for your unique brand of bittersweet folk-rock,” and Taylor isn’t exactly receptive.

He then performs “You’ve Got a Friend” while the astronauts float there helplessly, then does “Fire and Rain,” but changes the lyric “sweet dreams and flying machines in pieces on the ground” to “flying safely through the air.” In the DVD commentary, the writers admit their nervousness in pitching this scene to Taylor. The song is, after all, about the suicide of his childhood friend Suzanne Schnerr, but the artist was ultimately cool with it.

12: Barry White

“The minister of love, Larry White” (as Barry White is introduced by Mayor Quimby), shows up as the Grand Marshal of Springfield’s annual “Whacking Day” parade, an event where citizens gather to whack all the snakes in town to death. When White finds out what the festival is about, he’s horrified but agrees to do a favor for Lisa, telling her “Anything…for a lady”, and attracts the snakes into the safety of the Simpson’s home with a bass-heavy performance of “Can’t Get Enough of Your Love, Babe.”

11: Tom Jones

When Marge gets a job at the power plant, Mr. Burns seeks her advice on how to cheer up his dreary workforce, and she suggests healthier snacks, a Funny Hat day, and “piping in some Tom Jones music.” You then see the same employees still just as depressed but wearing funny hats, and “What’s New Pussycat” is blaring. Progress!

The episode takes a dark turn when Mr. Burns tries to seduce Marge by giving her a private Tom Jones concert, which involves Smithers knocking out the Welsh crooner with a suitcase of poison gas, then holding him at gunpoint.

When Homer stands up for Marge’s honor, Mr. Burns is impressed and rewards the couple with a private Tom Jones concert anyway, where he performs “It’s Not Unusual” while chained to the stage. He leans in to kiss Marge on the cheek and tells her, “get help, love – call Interpol, get me a hacksaw, anything,” then launches right back into the chorus, ever the true pro.

10: U2

When Homer runs to be Springfield’s sanitation commissioner, he sneaks onstage at a U2 concert by introducing himself to security as the “potato man,” and they immediately let him in.

His message is ill-received, though, and he’s pulled off the stage by security, with Bono assuring everyone, “don’t worry folks, he’ll get the help he needs.” The band then launches into “Pride (In The Name Of Love)” while Homer gets pummelled by security guards on the giant video backdrop.

The band also re-appears in a truly goofy post-credits sequence where Adam Clayton brags about his spoon collection.

9: Mick Jagger, Keith Richards, Elvis Costello, Tom Petty, Lenny Kravitz, and Brian Setzer

The Simpsons pulled in a who’s who of rockers for a Season 14 episode where Homer tries to recapture his squandered youth with a trip to Rock’n’Roll Fantasy Camp. Mick Jagger and Keith Richards give tips on showmanship (and micromanage the camp’s finances), Elvis Costello tries to sell them on playing bass, Lenny Kravitz talks crotch-stuffing, Tom Petty bores everyone with his symposium on “having meaningful lyrics,” and Brian Setzer has some wise words about the mighty guitar:

In the Simpsons’ Unauthorized History, Dan Castellaneta talks about how there was a built-in hierarchy among the rockers, with the Rolling Stones showing up 45 minutes late, Elvis Costello 30, Tom Petty, and Lenny Kravitz 25, and Brian Setzer right on time. He joked, “Michael Bolton came early, and he wasn’t even on the show.”

8: Bob Seger

Nothing quite covers up an OSEA citation quite like free Bob Seger tickets. After an incident at the Springfield nuclear power plant, Homer gets front-row seats to see the ‘Ramblin’ Gamblin’ man himself and brings along Chief Wiggum. The two ditch their wives to handle an overnight field trip with the kids and get scolded by Bob in the process: “a wife, like rock and roll, never forgets,” Seger tells them.

Episode 17 of Season 32, titled “Uncut Femmes,” also marks the first appearance of the chief’s wife, Sarah Wiggum (voiced by Megan Mullally), whose criminal past catches up with her, and she enlists Marge into an Ocean’s 8-like caper.

7: James Brown

Springfield brings in James Brown to headline their first (and last) Do What You Feel Festival, where he performs “I Got You (I Feel Good)” until a bandstand collapses behind him.

It’s short and not the funniest cameo in the show’s history, but it’s still just awesome and utterly surreal that James Brown was in The Simpsons at all.

6: David Crosby

David Crosby made two cameos on The Simpsons, once to give the Be Sharps (Homer’s barbershop quartet) their Grammy award:

And another as the AA sponsor to Lionel Hutz, the family attorney, who calls him in the middle of a trial to get talked off an urge for bourbon. Crosby, ever the gentle soul, tells Hutz: “Just take it one day at a time, and know that I love you.”

5: Paul & Linda McCartney

In “Lisa the Vegetarian,” one of the show’s all-time funniest episodes, Lisa finds some allies in her newfound animal activism: Paul and Linda McCartney, who like to hang out in Apu’s garden in the shade.

Paul also asks Lisa if she wants to hear a song, which turns out to be Apu shrieking an ungodly version of “Sgt. Pepper’s” while Lisa slinks away horrified.

4: Smashing Pumpkins, Sonic Youth, Cypress Hill, Peter Frampton

In one of the show’s all-time classic episodes, “Homerpalooza,” the middle-aged dad goes through the all-too-relatable dilemma of realizing that he’s become uncool. Or as Grandpa Simpson puts it (in a flashback), “I used to be with it. Then they changed what ‘it’ was. Now what I’m with, isn’t it. And what’s it seems weird and scary to me.”

Homer becomes the freak show “cannonball guy” for Hulabalooza and meets some 90s alt-rock staples from the height of the Lollapalooza era (and Peter Frampton):

When the cannonball act threatens his life, Homer decides remaining alive for his family is all that matters and gets booed off the stage and the tour, resigned to accept his permanently uncool status.

3: The Ramones

In maybe the single coolest moment in the history of the show, The Ramones regaled Mr. Burns with a terrifying, classically-Ramones-sounding rendition of “Happy Birthday,” ending with “go to hell, you old bastard.”

Mr. Burns responds with his iconic line: “Have the Rolling Stones killed.” Before Smithers can correct him, he adds, “Do As I Say.” Mr. Burns’ utterly horrified reaction to the performance is also one of the funniest little touches of animation in the show:

For the record, this was a later incarnation of the band. Joey and Johnny Ramone both did voices, but C.J. Ramone and Marky Ramone took the other two spots. Dee Dee Ramone and Tommy Ramone, the band’s original bassist and drummer, were gone by then.

2: Spinal Tap

Simpsons Swiss-army-knife Harry Shearer (who voices Burns, Smithers, Flanders, Reverend Lovejoy, Skinner, Kent Brockman, Rainier Wolfcastle, Otto, Dr. Hibbert, and thousands more) reunited with Christopher Guest and Michael McKean to promote Spinal Taps’ 1992 album Break Like The Wind by bringing the Tap to Springfield.

The show abruptly ends when Nigel gets blinded by a laser, and the band announces “Goodnight, Springton, there will be no encores” and walks off after 20 minutes, prompting a riot. Every scene with the band is almost like bonus footage from the cult-classic documentary, with some truly outstanding banter.

1: George Harrison

George Harrison’s cameo on The Simpsons remains one of the funniest guest spots of all time. When Homer’s barbershop quartet The Be Sharps skyrockets to fame, he attends a Grammy party, where he experiences the greatest thrill of his life. The show literally brought in a living Beatle just to record this:

He returns for one more line at the end of the episode, driving by to see the Be Sharps performing on a rooftop and simply declaring, “It’s been done,” and driving off. Total perfection.

Honorable Mentions: There’s easily another 30 you could throw on this list, but where to even start? The Who, Linda Ronstadt, Johnny Cash (who does the voice of a space coyote, so he’s not technically a musical guest), Sting, Elton John, Britney Spears, REM, Phish, Lady Gaga, Willie Nelson, Metallica, Fall Out Boy, The White Stripes, Ringo Starr. Name any musician, basically.